Aluminium lithium hydride → {2-[5-(1,1-Dimethyl-2-oxo-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester

HRID 1532385ノート

反応式

HRID 1532385 の反応式
[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([C:22](=[O:27])NCOC)([CH3:21])[CH3:20])[CH:17]=2)[NH:12][C:11]=1[C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[CH:29]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]([O:5][C:6](=[O:36])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([CH3:20])([CH3:21])[CH:22]=[O:27])[CH:17]=2)[NH:12][C:11]=1[C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[CH:29]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 56977920(2-{2-(3,5-Dimethylphenyl)-5-[1-(methoxymethylcarbamoyl)-1-methyl-ethyl]-1H-indol-3-yl}ethyl)carbamic acid tert-butyl ester

生成物 1

HCID 54043798{2-[5-(1,1-Dimethyl-2-oxo-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester収率 97.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (2-{2-(3,5-dimethylphenyl)-5-[1-(methoxymethylcarbamoyl)-1-methyl-ethyl]-1H-indol-3-yl}ethyl)carbamic acid tert--butyl ester (296 mg in 5 mL dry tetrahydrofuran) at 0° C. was added 1.8 mL of a 1M lithium aluminum hydride solution in tetrahydrofuran and the mixture stirred at low temperature. After 1 hour, the reaction was quenched by the careful addition of 0.3M aqueous a sodium bisulfate solution. The resulting mixture was extracted with ethyl acetate and the organic portion washed successively with 0.3M aqueous sodium bisulfate, water and brine. This was then dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography on silica gel (hexane:ethyl acetate, 85:15) to give the title compound (253 mg).

後処理

  1. customthe reaction was quenched by the careful addition of 0.3M aqueous a sodium bisulfate solution
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe organic portion washed successively with 0.3M aqueous sodium bisulfate, water and brine
  4. dry with materialThis was then dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography on silica gel (hexane:ethyl acetate, 85:15)

出典と根拠

ORDレコード
ord-777de129888944858c2dd2e70168c87f
出典データセット
uspto-grants-2001_03
特許番号
US06200957B1

反応ノート

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